1,4-Dithiane-2,5-diol as an efficient synthon for a straightforward synthesis of functionalized tetrahydrothiophenes via sulfa-Michael/aldol-type reactions with electrophilic alkenes |
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Authors: | Nikla Baricordi Simonetta Benetti Valerio Bertolasi Carmela De Risi Gian P Pollini Francesco Zamberlan Vinicio Zanirato |
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Institution: | 1. Dipartimento di Chimica, Via Luigi Borsari 46, 44121 Ferrara, Italy;2. Dipartimento di Scienze Farmaceutiche, Via Fossato di Mortara 19, 44121 Ferrara, Italy |
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Abstract: | ‘One-pot’ tandem reactions of commercially available 1,4-dithiane-2,5-diol (the dimer of mercaptoacetaldehyde) with electrophilic alkenes resulted in the facile formation of substituted tetrahydrothiophene derivatives. Thus, sulfa-Michael/Henry and sulfa-Michael/aldol sequences provided polysubstituted tetrahydrothiophenes using in situ generated nitroalkenes and α,β-unsaturated carbonyl compounds as the electrophilic partners of mercaptoacetaldehyde dimer, respectively. |
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